Sodium Iodide → N'-(2,4-difluorophenyl)-N-heptyl-N-[5-(6-nitro-1H-benzimidazol-2-ylthio)pentyl]urea

HRID 486085

反応式

HRID 486085 の反応式
[H-].[Na+].[I-].[Na+].[N+:5]([C:8]1[CH:9]=[CH:10][C:11]2[C:12]([CH:17]=1)=[N:13][C:14](=[S:16])[N:15]=2)([O-:7])=[O:6].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:25]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1[F:35])=[O:26]>CN(C)C=O.O>[F:35][C:29]1[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:28]=1[NH:27][C:25](=[O:26])[N:24]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][S:16][C:14]1[NH:13][C:12]2[CH:17]=[C:8]([N+:5]([O-:7])=[O:6])[CH:9]=[CH:10][C:11]=2[N:15]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 10342005N-(5-bromopentyl)-N'-(2,4-difluorophenyl)-N-heptylureaHCID 190975566-Nitrobenzimidazol-2-thione

生成物 1

HCID 9936925N'-(2,4-difluorophenyl)-N-heptyl-N-[5-(6-nitro-1H-benzimidazol-2-ylthio)pentyl]urea収率 337%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒3 回

実験手順

Part E. To a suspension of sodium hydride (0.04 g, 60% mineral oil dispersion, 0.001 mol; washed free of mineral oil with hexane) and sodium iodide (0.15 g; 0.0011 mol) in N,N-dimethylformamide (10 mL) under a nitrogen atmosphere, cooled to 0°, a solution of 6-nitrobenzimidazol-2-thione (0.975 g; 0.005 mol) in N,N-dimethylformamide (5 mL) was added slowly. The reaction mixture was stirred for 30 minutes and then a solution of N-(5-bromopentyl)-N'-(2,4-difluorophenyl)-N-heptylurea (0.42 g, 0.001 mol) in N,N-dimethylformamide (5 mL) was added. The reaction mixture was stirred for 1 hour and then allowed to warm to ambient temperature and stirred an additional 24 hours. The reaction mixture was poured into water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with water and brine, then dried over magnesium sulfate and concentrated to give a viscous oil. The product was purified by flash chromatography on silica gel eluting with hexane:ethyl acetate (75:25::v:v) to give the title compound (1.2 g, 0.00337 mol) as a solid, mp 120°-122°. 1H NMR (DMSO-d6) δ13.25 (bs,1H), 8.27 (bs,1H), 8.05 (d,1H,J=7.6 Hz), 7.91 (s,1H), 7.57 (d,1H,J=7.6 Hz), 7.4-7.3 (m,1H), 7.25-7.12 (m,1H), 7.0-6.8 (m,1H), 3.37-3.16 (m,6H), 1.85-1.72 (m,2H), 1.6-1.35 (m,6H), 1.27-1.1 (m,8H), 0.83 (t,3H,J=6.8 Hz).

後処理

  1. temperaturecooled to 0°
  2. stirringThe reaction mixture was stirred for 1 hour
  3. stirringstirred an additional 24 hours
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give a viscous oil
  9. customThe product was purified by flash chromatography on silica gel eluting with hexane:ethyl acetate (75:25::v:v)

出典と根拠

ORDレコード
ord-65183a1b232d4d3890f7fe496caad538
出典データセット
uspto-grants-1994_03
特許番号
US05290801

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